1-Methyl-4-(tributylstannyl)-1H-imidazole → [2-(1-Methyl-1H-imidazol-4-yI)-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl]-carbamic acid tert-butyl ester

HRID 720158Notes

Reaction equation

CO[C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:10]=[C:11]3[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]=1[C:12]=23)=O.C([Sn](CCCC)(CCCC)C1[N:33]=[CH:34][N:35]([CH3:37])[CH:36]=1)CCC>C1COCC1>[C:23]([O:22][C:20](=[O:21])[NH:19][C:9]1[CH:10]=[C:11]2[C:17](=[O:18])[NH:16][N:15]=[CH:14][C:13]3=[C:5]([C:3]4[N:33]=[CH:34][N:35]([CH3:37])[CH:36]=4)[NH:6][C:7]([CH:8]=1)=[C:12]23)([CH3:25])([CH3:24])[CH3:26]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of intermediate 147(d) obtained from example 147 (184 mg, 0.5 mmol), 4-(tributylstannyl)-1-methyl-1H-imidazole (223 mg, 0.6 mmol) and Pd(PPh3)Cl2 (35 mg, 0.05 mmol) in THF (3 mL) was heated in a microwave oven (Personal Chemistry) for 2 hours at 130° C. The mixture was concentrated and the residue was purified by silica gel chromatography (5% MeOH/EtOAc) to give the title compound (110 mg, 0.289 mmol) in 59% yield as an orange powder.

Workup

concentrationThe mixture was concentrated
customthe residue was purified by silica gel chromatography (5% MeOH/EtOAc)

Sources & evidence

ORD record: ord-9bee9b316a044b6ead22c8494662290c
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07132533B2

Reaction notes

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